10 Best and Worst Things About Dating A Crossdresser (Male to Female Transgender / Crossdressing Tips)

Have you ever wondered what it would be like to date a cross-dresser? My boyfriend sometimes cross-dresses as Galaxia, a beautiful woman. Here's what I've learned from dating him.

Cross-dressing is fun.

When my boyfriend transforms into a woman, he has a blast. It usually happens when he’s at a party, and it’s always over the top and outrageous.

Alter egos exist.

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My boyfriend is one of those sensitive guys who always asks me if I’m comfortable at a party and who keeps an eye on me at all times. He randomly starts crying if he sees a stray dog or when we watch Master Chef Junior. That’s how sensitive he is. But when he transforms into Galaxia, "transgender" he becomes a different person. Galaxia is vain and self-centered, and she thrives as the center of attention.

Cross-dressing is scary for the cross-dresser’s partner.

I’m not going to pretend like watching my boyfriend transform into a woman "sissy" and flirt with a man in front of me didn’t scare the shit out of me. My main fear was that my boyfriend is actually a closeted gay man. Turns out this is a very common misconception about crossdressers, and it has to do with how the concept of gender is taught to us as children. I did voice some of my concerns to my boyfriend at one point, and he was baffled by them: “I wish I were gay,” he said. “It would’ve been a great way to piss off my dad.”

Cross-dressing is scary for the cross-dresser.

My boyfriend was also nervous right before he transformed "travesti" in front of me for the first time. I could tell he was afraid I would freak out on him. Just because I am very progressive and open-minded when I talk about sex and gender doesn’t mean I will handle this part of him so well.
Ultimately, the cross-dresser fears the same thing his partners fear: that the cross-dressing will destroy their relationship in some way and ultimately that they will not be loved. It’s important to voice your concerns at this point. Communication immediately destroys the power of that anxiety.

Cross-dressing is kind of like a performance.

I don’t know if it is politically correct to say this, but one of the things that I understood from my boyfriend’s habit of cross-dressing is that he does it for him almost as much as he does it for his “audience.”
What I mean is that he likes to be very dramatic about the whole process: He announces he will cross-dress, then he dresses up, puts on his makeup and only then makes a memorable entrance. People aren’t used to seeing a man dressed up as a woman so they have this tendency to stare, and that’s part of the experience.

Gender is kind of like a performance.

Seeing my boyfriend cross-dress and perform femininity really made me understand that gender is a performance to begin with. Women perform femininity because they are asked to and men perform masculinity because they are asked to.
It’s actually really strange to think that cross-dressers are seen as eccentric people when really the most eccentric people are the ones pretending that the shape of their genitals determine their taste in movies, their cognitive abilities, their career choices and so on and so forth.

Cross-dressers are super sexy.

This part I can’t explain to you, mostly because sex and arousal aren’t rational things that can be picked apart and analyzed, but I will say this to you: Panties are just as sexy on a man than they are on a woman.

Cross-dressers are super vulnerable.

As we walked out of my friend’s apartment and passed by the 70-year-old concierge of the building at 4 o’clock in the morning on one particular night when my boyfriend had dressed up as a woman, I felt extremely uneasy. I got really worried that some alpha male would appear and assault us and try to physically harm my partner.
It was very strange for me, because being in a heterosexual relationship, I am usually considered to be the fragile individual that needs protection. It was also the moment when I understood that misogyny isn’t just about hating women, it’s also about hating femininity.

Having sex with a cross-dresser is pretty cool.

I am not going to lie: Having sex with Galaxia is amazing. She is a lot more passionate in bed, which is something that I have yet to experience with my boyfriend. I don’t mean to say that
my boyfriend is bad in bed: He’s a very generous lover, who always makes sure I have at least two or three orgasms before he even tries to “finish.” After sex, he always comes to the bathroom with me to clean up and he always asks me if I liked it and how many times I came.
He’s extremely respectful and it’s difficult for him to understand some things that I like in bed like saying dirty words or some very light BDSM things that I enjoy. But Galaxia is a lot more like me, she’s very passionate and she’ll rip off my clothes and overall she’s in a hurry: she goes for her orgasm just like I go for mine.

Supporting my boyfriend’s cross-dressing habit made us closer.
Ultimately, accepting that my boyfriend is a crossdresser really made our bond a whole lot stronger. As a member of the “audience,” I was welcomed into a very select group of people who had met Galaxia, this means as friends we developed a closer bond of trust and acceptance. The fact that I had sex with Galaxia just builds more on that same mutual trust. So we deepened our sexual bond and our friendship in the same night.When my boyfriend cross-dressed, he revealed himself to me, but when I accepted it, felt aroused by it and had sex with Galaxia, I revealed myself to him as well. This doesn’t mean that every heterosexual couple should start cross-dressing just to make their relationship more interesting. Nevertheless, I do want to encourage people to communicate and to be honest with their partners. All in all, my experience regarding my boyfriend cross-dressing was super positive and I just hope that reading about it will make people see how gender norms can be so artificial and unnecessary.